


The Boss' Songbird

by blue_skyes



Category: jacksepticeye, youtube - Fandom
Genre: Alternate Universe - 1920s, Cunnilingus, F/M, Lemon, Mafia AU, Smut, Vaginal Fingering, Vaginal Sex, period fic
Language: English
Status: Completed
Published: 2018-01-07
Updated: 2018-01-07
Packaged: 2019-03-01 13:21:18
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,314
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13295745
Author URL: https://archiveofourown.org/users/blue_skyes/pseuds/blue_skyes
Summary: It's almost 1920 and you're a singer at one of the most famous clubs in New York City. Your career is booming, and you wouldn't change it for the world. Except when the Irish mafia show up to see you perform, and The Boss wants to meet you after. Will he be the one to change your mind?





	The Boss' Songbird

**Author's Note:**

> Hey there guys! So I was inspired to write this fic based on these edits I had seen on tumblr: https://number1fanofsam.tumblr.com/post/169391470521/a-friend-of-mine-wanted-to-see-anti-in-a-suit-and
> 
> I hope you guys enjoy it!
> 
> Songs used as inspiration:  
> We Found Love and Toxic, both by PostModern Jukebox!

You sat in your dressing room, powdering your face and finishing off your makeup for that night’s show. You were the main singer in one of New York’s biggest clubs, and people flocked to the club each night just to see one of New York’s rising stars. Your hair was perfectly styled, hanging in loose wavy curls, and a shining headband with a pristine white feather wrapped around your head. Once your makeup was done, you got dressed, slipping on your favorite (f/c) gown, floor length and covered with sparkles. Your love of shine, and the outfits you wore, along with your silvery light voice, the people of New York called you their shining star. Though you received countless letters and flowers from men all across the city, you left them ignored. You enjoyed the praise you received, but your career was something you favored more, plus, there was the fact that you hadn’t seemed to find someone who piqued your interest yet.

You were so close to stepping on stage, standing in the wings, when you jumped, feeling a hand touch your shoulder. Turning around, you breathed a sigh of relief at the sight of your boss, the owner of the club. “Hey there Johnny, what’s the news?”

Johnny smiled at you, but you could see the wary and nervous look in his eyes. “Big news darlin’. We got a special guest tonight, and I want you performing at your best!”

“A special guest?” You gasped. “Well, who is it?”

Johnny looked at you right in the eyes, but hesitated to answer.

“C’mon Johnny! Don’t keep me waiting!” You whined, your curiosity taking over you.

“Well,” Johnny leaned in close, his voice a whisper as he spoke to you. “The Irish Mafia’s here, and the Boss came with them!”

Your eyes widened at Johnny’s words. “The Boss?!” You couldn’t hold your shock as you almost yelled the words.

“Hush!” Johnny said, gesturing for you to lower your voice. “Yes, _The_ Boss is here. That’s why you gotta be at your best tonight. Who knows what they’ll do to this place if you don’t do well! Now good luck!”

Johnny turned and walked off, leaving you standing there with your thoughts. It was almost 1920, the year at its end, and the Irish mafia was at its biggest, and it seemed they were only going to get bigger from there. They were the biggest and most threatening group in town, and if you ever did them wrong, they made sure you weren’t ever going to forget it. And The Boss himself was the one no one certainly wanted to mess with. Rumors flew around the busy city, they said he was unkillable. That anyone who did anything he didn’t like died a gruesome and terrible death. And you definitely didn’t want to risk any of that happening to you or anyone else at the club.

So you took a deep breath in, calmed your thoughts, smoothed your dress, and walked out on stage, as prepared as you ever would be to give the best performance of your life. As you stepped out on stage, the spotlight shone directly on your face, and despite the bright lights, you could still see the mafia, all of them sitting in the back, most prominently The Boss, sitting in the middle of them, his deep, almost pitch-black eyes watching you intently. You took another deep breath in, and signaled for the band that you were ready to start, before singing your heart out.

The entire night, you sang mostly more upbeat songs, getting the crowd dancing, before slowing down and singing some love songs, letting the people who had either come with or found a partner time to enjoy some quality time with their partner. You tried your best to ignore The Boss in the back, but you couldn’t help but feel his eyes on you the entire night, and it was slightly unnerving. But you powered through your set, and once you were finally done for the night, you smiled and waved, looking over the crowd, and you saw that The Boss had stood, giving you a standing ovation. You hoped that your blush wasn’t visible through the lights, and took one final bow before heading backstage to your dressing room.

Sitting at your mirror, you sighed in relief, glad that your show was over and that everything seemed to have gone well. It wasn’t long that you were in there, when there was a knock on your door. You sighed and rolled your eyes, expecting to see more flowers and letters from your admirers. Instead, it was your boss Johnny again. “What is it this time Johnny?” You huffed.

Johnny gulped, looking at you with eyes full of fear. “I-It’s the Boss (Y/N). H-He wants to see you over at the bar. N-Now.”

You weren’t about to say no to The Boss, so you silently nodded, and quickly touched up your makeup before stepping out into the club. You put on your most confident air, and walked over to the bar, where you saw The Boss, sitting on his own. You were finally able to get a good look at him, and noticed that his hair seemed to have a slightly green tinge to it, and he was wearing a deep purple suit. You sidled in on the seat next to him and cleared your throat softly, in order to get The Boss’ attention. “You asked for me, Mister The Boss, sir?” You said to him, in the sweetest voice you could muster despite your fear.

The Boss looked over at you, and he smirked as he looked you up and down. Meeting his gaze, as he looked back up at you, you could tell there was something about him. Something different than your other admirers. And whatever it was, it had you completely intrigued. “I did indeed, doll. You put on a great show tonight. Your voice is just as incredible as told. And by the way, no need for formalities. Call me Anti, please.”

“W-well thank you Anti…” You blushed, tucking a stray hair behind your ear as you averted his gaze. The Boss, or Anti, as he wanted you to call him, placed a soft touch on your chin, tilting your head up so that you would look at him once more.

“No problem babydoll, but tell me, what’s your name? It’s only fair I know your name if you know mine.” That smirk was still plastered to his face, and it was a look you almost couldn’t resist.

“It’s (Y/N). (Y/N) (L/N).”

“(Y/N)…” Anti contemplated your name for a moment, before smiling at you once more. “Your name truly reflects your beauty (Y/N).” He took a hand of yours in his, and placed a soft kiss to it, making you blush even more.

“Anti… You flatter me.”

“I’m simply being truthful. I don’t think I’ve ever seen a lass as beautiful as you.” Anti’s gaze was becoming more intense, and the more he spoke to you, the thicker his Irish accent seemed to become.  He quickly downed the rest of his drink, taking a sharp intake of breath before moving to speak to you once more. “You know (Y/N), this joint seems a bit crowded eh? Why don’t we go somewhere a little more…” Anti leaned in close to you, whispering in your ear. “Private? Hmm?”

Anti’s breath against your ear made you shiver, and despite the warning bells going off in your head of how dangerous he was, you couldn’t help but feel like you were starting to fall for him. “Yes…” Your voice was a whisper that matched his own, and you nodded, to emphasize your response.

“Good girl. That’s just what I like to hear.” Anti smirked at you, before taking your hand in his once more, and leading you out of the club. He led you over to his car, where he opened the passenger side door for you, letting you slide in before shutting the door and getting in on his own side.

“So… where are we goin’?” You asked as Anti pulled away from the club and off into the night.

“We’re goin’ back to my place. If you’re alright with that, that is…” Anti gave you a mischievous glance, placing a hand on your thigh and giving it a squeeze. You knew exactly what he was insinuating, and you honestly didn’t mind. If it were any other man, you would have pushed his hand off of you and made him stop the car. But the thought of being with the Boss of the biggest mafia group in New York thrilled you. There was a danger to it, and you were excited to find out more.

“O-Of course!” You tried to smooth your voice, but it really had done nothing to ease your enthusiasm. Anti gave your thigh one last squeeze with a chuckle, before continuing on driving.

It wasn’t long until you reached the outskirts of town, coming up to what looked like a beautiful manor. “Wow…” you whispered to yourself.

“This is my home.” Anti beamed proudly. “Like what you see?” You nodded in return, not able to say much else. “Well hopefully you’ll like what else I have to show you.” Anti licked his lips, winking at you as he parked his car. “Come with me.” He escorted you out of the car, and inside his manor.

The inside of the house was just as beautiful as the outside, though you weren’t allowed to linger for long, as he was already leading you up the stairs and to his bedroom. Anti’s bedroom was opulent, to say the least, with a wall of windows overlooking a lake, an enormous bed against one of the walls, with expensive paintings covering the walls. You followed Anti as he led you to his bed. “So (Y/N), doll, I was maybe hoping you could… give me a private show? One we could turn into a duet maybe?” He smirked at you, and you knew exactly what he meant.

Anti was running his hands up your arms, moving them to grip your hips. You were getting more and more excited by the moment, and you couldn’t help but let out a soft moan as he felt your body.

“So you do want it, hmm?”

“Oh god yes!” You breathed out, wrapping your arms around Anti’s neck to pull him closer. He knew exactly what you needed, and placed his lips roughly against yours, kissing you passionately and desperately. You ran your hands through his hair, tugging slightly at it, eliciting a moan from him.

After a moment, Anti pulled away from you and began undoing your dress. “What say you we slip this off, hmml?”

You nodded, and turned away from him, so that he had better access to your dress as he removed it. Once it was off, you stepped out of your heels and turned to face him. You could see Anti smirk as he noticed you weren’t wearing a bra underneath, and only wore a pair of lacy panties instead. “What a beautiful sight you are, babydoll. Perfect breasts…” Anti’s voice trailed off at the end, as he took his breasts in yours, squeezing them with just the right amount of pressure to elicit a moan from your lips. “Oh yes… good girl. Singing for me already…. Let’s see how else we can make you sing…” He laid you backwards on his bed, and took off his suit jacket, rolling up his shirt sleeves as he tossed the jacket aside. Anti climbed over you on the bed, looking you straight in the eyes. “Though I do have one more thing before we continue, dear (Y/N).”

“W-What is it, Anti?” You wanted to look away from his gaze, but you felt like your gaze was completely locked with his and you were unable to look anywhere else.

“You know how the rumors say I’m unkillable, right?” You nodded, wondering where he was going with his story. “Well it’s **_true_**.” Anti’s voice got deeper as he spoke, and you watched as his eyes went from normal human eyes, to eyes as dark as the night sky.

You gasped at the transformations, not knowing what to think. “I-I…. Anti, you’re a-”

“That’s right doll. I’m a demon. How else do you think the mafia got so powerful?” Anti smiled at you, revealing two fangs you hadn’t noticed before. “Are you… scared?” He growled, close to your ear.

“N-No.” You stuttered a little, but quickly regained your composure. “I want to learn more about what you can do.”  
“Well then… In that case, let me show you.” Anti growled, before planting another rough kiss to your lips. You couldn’t help but moan as he held you down, slipping his tongue inside your mouth. You were intoxicated to the taste of him, and you couldn’t wait to see what else he could do.

Not long after, Anti pulled away, and before you could even protest, you let out a loud moan as he bit down hard on your neck. You could feel him sucking slightly, clearly tasting your blood. Anti quickly moved from the bite, stopping himself before he went too far. “God you taste delicious doll… I can’t wait to make you ** _mine._** ” The way he growled out that last word made you shiver, and you wanted more of him. Hoping to get rid of some of your frustrations, you wriggled your hips against him, hoping to get some of that desired friction you craved. Upon noticing what you were doing, Anti’s hands gripped your hips hard, holding them in place and stopping you from moving them. “Ah-ah-ah… you must be patient dear. Good things come to those who wait.” You pouted, but that look on your face was soon replaced, as Anti moved his mouth and began sucking on one of your nipples out of nowhere, making you gasp. He played with your other breast, before switching the two, and you were loving it. But just as quickly as he started, he abruptly stopped, moving down closer and closer to your legs.

Anti spread your legs roughly, placing nips and kisses along one, all the way up it, but conveniently skipping over the one spot you so desperately craved, before moving straight to your other thigh, giving it the same treatment as the first. Moving back towards your center, Anti couldn’t help but let out a soft moan as he looked at how soaked your panties were for him. “Oh yes babydoll… I can’t wait to taste you and make you sing for me…” He slipped off your panties in one fell swoop, and seeing how wet you were, he instantly moved in and licked a teasing stripe up your vagina, making you moan. “Yes… good girl… sing for me, my little… songbird.” Anti began licking and sucking at your clit, making you go wild. The teasing licks made you moan louder, and your body arch. This was a sight Anti was reveling in, loving every noise and every move you made.

Anti then made the brave move of thrusting two fingers right inside you, and you could have almost jumped right into the air, with the shock of them inside you. They slipped in easily, considering how wet you were, and you could feel Anti smirk against you as he began thrusting them in and out. It wasn’t long until you were close and Anti could tell. “A-Anti… I’m almost- gonna-” But before you could, Anti completely stopped what he was doing, and pulled away. You whined, pouting at him.

“Now, now dear, I want you right on that edge when I push myself inside you. It’s going to feel much better for the both of us, I promise you.” That made your pout slightly disappear, and Anti stepped back, fully undressing himself now, before crawling above you once more. “Are you ready doll?” Anti asked, rubbing his erect cock up and down your vagina, teasing your hole as he did.

“Y-Yes please Anti! Please fuck me! I _need_ you inside me!” You bucked your hips against his, hoping to get him to slip inside you, to no avail.

Anti chuckled, “I do love hearing you beg doll, it’s almost as beautiful as when you sing.” Taking you off guard once more, he thrust himself inside you, making you moan loud and long.

“O-Oh god yes Anti!” you could feel the way he filled you up, making you feel perfectly full inside as he went all the way down to the hilt. Your hips twitched against him, and he groaned at the feeling.

“Babydoll… oh how I love feeling your walls pulse around me. Gripping me, holding me deep inside you. I can feel your desire pulling me in as deep as I can go. And it’s wonderful.” Anti growled, beginning to thrust into you. Hard, but slow, letting you get used to the feeling before picking up the speed. You began matching his thrusts with your hips, slamming them into his as they met. The two of you were moaning and writhing against each other, the contact of his skin on yours making you feel more alive with each thrust.

“A-Anti….” You groaned in his ear, wrapping your arms around him to hold him close. “I’m getting close again…”

Anti picked up the pace at your words, and he was beginning to drive you mad. “Don’t come yet doll. Hold that for me. Stay right on that edge. Wait for me. I want to cum with you.” You continued at your pace, and you could tell that Anti was getting close as well, as his thrusts became harder and more erratic.

You were moaning incoherent phrases into Anti’s ear, “ _Faster, harder, more… I need…_ ” and Anti obliged.

“I’m gonna cum inside you doll... fill you with me, make you **_mine_**.” Anti said, shifting his angle to properly hit your gspot. “A-almost there doll,” He said, voice slightly shaking as his orgasm approached. “I’m gonna count to ten and then we’re gonna cum, alright?”

“ _Please!_ ” You whined, not sure how much longer you could hold your orgasm back. Anti began to count, though much too slow for your taste, but when he finally reached ten, you moaned louder than you ever had, the feeling of your orgasm rushing through you as you came, your cum covering Anti’s cock as he filled you with his seed.

The two of you lay there panting, thrusting against each other as you both rode out your orgasms, once you both came down from your orgasmic highs, Anti reluctantly pulled out of you, rolling over to his side and pulling you flush against him. “So, (Y/N), doll, I’ve got an offer for you.” You nodded, listening intently. “I’ve realized that after tonight, I don’t quite wanna let you go. So why don’t you quit your job, and come be my girl instead? I’ll give you anything you want, all the money and jewels you could ever dream of, and you wouldn’t have to do a thing but be mine, forever.”

You had always said to yourself that you would never give up your career for a man, but Anti, you found, was no man. He was a demon, and you knew then and there that you wanted him just as much as he wanted you. And as much as you loved singing, you knew you’d be happy being his for the rest of eternity. “Yes.” You replied breathily, nuzzling your face in his chest, as you felt yourself fill with joy.

“That’s just what I wanted to hear…” Anti chuckled slightly, as he kissed the top of your head. “My little songbird…”

**Author's Note:**

> If you guys got this far, thank you for reading till the end! I really do appreciate everyone of you, and I would be eternally grateful if you left me a kudos or a comment if you enjoyed reading this fic as much as I loved writing it! And if you didn't I'm always down for constructive criticism, and I'd be glad if you could let me know what it was you didn't like in the comments, so that I can improve and grow with my writing. :) Thank you once again for reading this, I love you all!


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